(2S,6R)-6-[(S)-1-({(2S,6R)-6-[(S)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbonyl}-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl ester | 444687-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,6R)-6-[(S)-1-({(2S,6R)-6-[(S)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbonyl}-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl ester
• 英文别名: ethyl (2S,6R)-6-[(1S)-2-[tert-butyl(dimethyl)silyl]oxy-1-[[(2S,6R)-6-[(1S)-2-[tert-butyl(dimethyl)silyl]oxy-1-(phenylmethoxycarbonylamino)ethyl]oxane-2-carbonyl]amino]ethyl]oxane-2-carboxylate
• CAS: 444687-41-6
• 化学式: C₃₈H₆₆N₂O₉Si₂
• 分子量: 751.121
• InChiKey: HOWUPCURZDLNDY-YVHQNKTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.25
• 重原子数：
  51
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,6R)-6-[(S)-1-({(2S,6R)-6-[(S)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbonyl}-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成 (2S,6R)-6-[(S)-1-({(2S,6R)-6-[(S)-1-Amino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbonyl}-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and Structure of Preorganized, C₃-Symmetric Trilactam Scaffolds with Convergently Oriented (S)-Acetylthiomethyl Appendages

  摘要：

  Efficient modular synthesis of conformationally preorganized, C-3-symmetric trilactams is reported. The allyl acetate cyclization substrate was synthesized in five steps from Gamer's L-serine-derived aldehyde. After chiral ligand-mediated palladium cyclization, the resulting vinyl hydropyran was transformed into the orthogonally protected amino acids for iterative coupling. The final macrolactamization was accomplished using EDCI/HOBt or HATU/HOAt under high dilution conditions.

  DOI：

  10.1021/ol0261480
• 作为产物：
  描述：

  (S)-4-[(Z)-7-(tert-Butyl-dimethyl-silanyloxy)-hept-5-enoyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester 在 palladium on activated charcoal 咪唑 、 2,6-二甲基吡啶 、 (S,S)-DACH-phenyl Trost ligand 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 sodium hypochlorite 、 sodium dihydrogenphosphate 、 cerium(III) chloride 、 zinc(II) tetrahydroborate 、 2-甲基-2-丁烯 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 氢气 、 1-羟基苯并三唑 、 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 叔丁醇 、 苯 为溶剂， 反应 99.0h， 生成 (2S,6R)-6-[(S)-1-({(2S,6R)-6-[(S)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbonyl}-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and Structure of Preorganized, C₃-Symmetric Trilactam Scaffolds with Convergently Oriented (S)-Acetylthiomethyl Appendages

  摘要：

  Efficient modular synthesis of conformationally preorganized, C-3-symmetric trilactams is reported. The allyl acetate cyclization substrate was synthesized in five steps from Gamer's L-serine-derived aldehyde. After chiral ligand-mediated palladium cyclization, the resulting vinyl hydropyran was transformed into the orthogonally protected amino acids for iterative coupling. The final macrolactamization was accomplished using EDCI/HOBt or HATU/HOAt under high dilution conditions.

  DOI：

  10.1021/ol0261480